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Hotels in Chester

Choose from 3084 Chester Hotel Deals

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
  • 1 min walk from DaVallia Art & Accents
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8.2/10 Very Good! (436 reviews)
"Beautiful old inn Great Staff"

Reviewed on Jun 7, 2026

Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
  • 1 hour drive from DaVallia Art & Accents
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (582 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."

Reviewed on May 22, 2026

Woodstock Inn & Resort
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
  • 59 min drive from DaVallia Art & Accents
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (848 reviews)
"dirty room and overcapacity. No breakfast"

Reviewed on Jun 2, 2026

Kimpton Taconic Hotel by IHG
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
  • 1 hour drive from DaVallia Art & Accents
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (894 reviews)
"Charming and clean with helpful people who checked in before we got there to get to make sure we knew how things worked with checking in and keys and such. It’s dated, but it appears as if they’ve renovated and cleaned things up to look and feel beautiful as well and be functional."

Reviewed on Jun 6, 2026

Latchis Hotel
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
  • 1 hour drive from DaVallia Art & Accents
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (1,002 reviews)
"Average at best- very dated and so noisy throughout the night. Couple lights didn’t work, definitely no frills, but if you can suck it up for one night, it’ll do."

Reviewed on May 31, 2026

Days Inn by Wyndham Keene NH
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
  • 1 hour drive from DaVallia Art & Accents
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
8.2/10 Very Good! (989 reviews)
"We had a reat stay. Hotel was vey clean and staff was. Very helpful"

Reviewed on Jun 1, 2026

Hampton Inn Brattleboro
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
  • 1 hour drive from DaVallia Art & Accents
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (932 reviews)
"Th peaceful sitting area near the river was ideal for enjoying a nice night by the fire. The perks of camping but with a real bed!"

Reviewed on Jun 1, 2026

The Shire Woodstock
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
  • 59 min drive from DaVallia Art & Accents
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are ...
8.6/10 Excellent! (271 reviews)
"I was traveling for work and needed a place to stay for one night while I was in the area. The rooms were very outdated and pretty beat up. There was a deck attached to my room and the door didn’t even lock to the deck. It was very warm outside during my stay as well and the air conditioner in my ..."

Reviewed on Jun 7, 2026

Grand Summit Resort, A Vail Resorts Property
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
5383 Main St Manchester Center VT
  • 56 min drive from DaVallia Art & Accents
Book a stay at this golf hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (940 reviews)
"Gentleman that checked us in was very friendly and helpful. Breakfast was typical continental breakfast and was good. Had two rooms, first room was fine. Clean but air conditioning did not work. Second room, heat did not work and our first night was cool out. They did move the second room. Heat worked ..."

Reviewed on Jun 7, 2026

The Palmer House Resort, an Ascend Collection Hotel
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
  • 58 min drive from DaVallia Art & Accents
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,002 reviews)
"Great stay. Beautiful location"

Reviewed on Jun 6, 2026

On The River Inn
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
  • 1 hour drive from DaVallia Art & Accents
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (1,002 reviews)
"Was decent"

Reviewed on Jun 6, 2026

Best Western Plus Keene Hotel
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
  • 59 min drive from DaVallia Art & Accents
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American ...
7.4/10 Good! (634 reviews)
"I’ve stayed here before and I’m glad I returned. The staff is friendly. I ate dinner at the bar after a long day. The filet was cooked as requested and the asparagus was fresh. I made use of the pool the following morning. My stay was perfect."

Reviewed on Jun 5, 2026

The Equinox Golf Resort & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find cheap hotels in Chester

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